Cheshire Cobbles via Appalachian Trail

MODERATE 36 reviews

Cheshire Cobbles via Appalachian Trail is a 2 mile moderately trafficked out and back trail located near Cheshire, Massachusetts that features beautiful wild flowers. The trail is rated as moderate offers a number of activity options. Dogs are also able to use this trail but must be kept on leash.

2.0 miles
816 feet
Out & Back

dogs on leash

kid friendly





nature trips



wild flowers



2 months ago


2 months ago

This is a short hike with lots of steep spots scattered throughout (nothing terrible). The trail markings are sad, but the rock features and view at the top are worth it.

3 months ago

Favorite trail

3 months ago

Short trip to the top and a bit steep, but very manageable. Can take anywhere from 30 min-1 hr to reach the cobbles, depending on level of fitness and break time. Great view of Cheshire Lake and Mt Greylock. Great spot for sunset too, just bring a light for the trip back down!

8 months ago

Cool spot.

10 months ago

Park at the Ashuwillticook Rail Trail parking area, 41 Railroad St., Cheshire, MA 01225 (this address is how Google maps marks it, I don't know if the address is actually marked on the ground). It's across the street from the Cheshire Post Office. Parking is free.

It's a nice little hike, first through a residential area of a small town, then through woods most of the way. It starts out fairly gradual and gets a little steeper toward the end. The view of the surrounding mountains and valley dotted with small villages and a lake is lovely.

Hike directions: From the rail-trail parking lot, head east on Main St. You'll pass a giant "Cheshire Highway Dept." snowplow monument on the right, and then a small ice cream shop on the left. Where Main St. and East Main St. come in together, take East Main to the right, and in about 200 feet, turn right uphill onto Furnace Hill Road. Follow for about 1/3 mile until you see the white blazes turn uphill to the left, where there are woods on both sides of the street. The turn should be marked.

The route uphill is mostly quite wide, and starts out gradual. Follow the rectangular 2" x 6" white paint blazes on trees. Double blazes usually indicate a turn. If the blazes are offset (uneven) turn in the direction of the upper blaze. When you are almost at the end, you'll see a big rock outcropping. You'll continue past it, and then take a blue-blazed side trail that passes through mountain laurel a few hundred feet to the overlook. Enjoy the view, and return the way you came.

11 months ago

Hi; can someone please tell me the physical address to drive to the Cheshire cobble trail?

Monday, July 03, 2017

It is a great little hike from Furnace Hill Road. It is also a great spot to watch the locals fire off fireworks around the "forth."

Saturday, May 13, 2017

Beautiful view!!! Follow the white markers. Best to use GPS from alltrail app due to some of the trail is poorly marked.

Tuesday, April 25, 2017

Views were awesome!

Friday, October 07, 2016

Great short hike! Not as steep as I would have expected. Took about 1.5 hrs round trip with 15 minutes at the top, and parking at the rail trail parking in Cheshire. No parking at trailhead. Return to Cheshire by AT North- white blazes, trail has a few turns so keep an eye for blazes. Views were awesome at the top!

Sunday, September 11, 2016

Short, steep trail leading to fantastic views to the north, west and south.

Monday, August 08, 2016

Parking area is on Notch Rd.

Saturday, June 25, 2016

Google maps via this app brings you to the end of Furnace Hill Road, a residential area with no parking sides on both sides of the street. Can someone please post where the parking is for this hike?

Sunday, May 15, 2016

when you get to the red arrows pointing back the way you came, follow them backward and around to the left away from the AT for about 100 ft.

Thursday, April 28, 2016

Gorgeous view and perfect workout

Friday, April 22, 2016

The scenery was beautiful. The hike was very pleasant. Will do it again for sure. Had a awesome picnic on the top of the cobble looking out at Cheshire Lake.

Wednesday, March 30, 2016

Great views. Got lost on the way up. Follow single white markers not the double when you come to the fork.

Monday, November 02, 2015

Beautiful hike with amazing views

Sunday, October 18, 2015

Cold, short hike. Steep incline but overall easy hike. The view is spectacular.

Friday, April 03, 2015

Accessed via the AT. Absolutely beautiful views. Greylock is visible in the distance on a clear day.

Thursday, November 06, 2014

just hiked this trail for the first time. The view was so awesome. Plan to again soo.

Friday, May 09, 2014

First time on the trail and I loved it! I am going to do this trail more often. The hike up the hill was rough for someone out of shape but it was worth it for the view! The view was better than I thought. I could of stayed up there for hours.

Monday, December 09, 2013

Good parking and access. You'll follow a footpath until hits the Appalachian Trail that is marked by signs and yellow paint/markings, I believe you're suppose to follow the AT up to the overlook. I got side tracked by the multiple trails, footpaths and logging trails, so be careful.

Wednesday, October 02, 2013

fantastic views from the top. took about 45 minutes to get up and back. a little on the steep side but worth it.

1 month ago

1 month ago

4 months ago

Wednesday, June 21, 2017

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